


Smitten With You

by HalfwayToHell



Category: Supernatural RPF
Genre: Anal Fingering, Anal Sex, J2, M/M, bottom!Jared, sugardaddy!Jensen, top!Jensen, twink!Jared
Language: English
Status: Completed
Published: 2016-04-06
Updated: 2016-04-06
Packaged: 2018-05-31 00:37:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,376
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6448528
Author URL: https://archiveofourown.org/users/HalfwayToHell/pseuds/HalfwayToHell
Summary: <blockquote class="userstuff">
              <p>When thirty-year-old billionaire Jensen Ackles attends a charity event, the last thing he expects is for something so delicate, so beautiful to catch his attention, but it was not a something--more like a someone. Twenty-year-old college kid Jared Padalecki, an escort of all things. Jensen could have anything he wanted in the world with the kind of money he had, but the thing he wanted most, was the beautiful college boy.</p>
            </blockquote>





	Smitten With You

**Author's Note:**

> I do accept prompts via my Tumblr account: http://hes-my-brother.tumblr.com/  
> I accept Wincest/J2/Swesson prompts; any and all kinks are accepted.

* * *

 

The first time Jensen saw him, was during a charity event--what association he couldn't for the life of him remember, but that had not mattered. What had mattered and what still mattered was the boy he had seen there. It was more of a glance, one that had lasted a fraction longer than he had initially intended.

 

But how could he _not_ notice? How could he _not_ stare a fraction longer?

 

The boy seemed to be at a minimum ten years younger than Jensen--who was thirty, making the boy at his youngest to be twenty. The boy had been standing at least ten feet away from him and wore tight-fitted jeans and a forest green button down shirt. His chestnut hair was long enough to cover the tops of his ears and swept across his forehead.

 

The boy feigned his interest in the event in the way that he stood, his hip cocked out and his arms folded across his chest. One of his hands had been playing with the brown leather cord necklace snug around his throat, subconsciously fingering it and he couldn't help but wonder if that was something he did often.

 

Jensen found that he could not blame him. After all, many escorts were brought to events such as charities or dinner parties and so most of them had grown used to the redundancy of the posh environment--as well as the people.

 

He had been so lost in his staring, that it took him a moment to realize the boy was currently watching him, still fingering his necklace. The boy's blue-green--no hazel--no that wasn't quite right--Jensen was unsure of what shade of eyes the boy had because they seemed to change color under the conditions of the lights or in the way he moved them.

 

In the end, it had not mattered because the boy was looking at him, _inspecting him_ with his kaleidoscope gaze. His eyes had traveled leisurely down the length of his body--which gave him the indication that the boy was incredibly confident--before flicking back up to meet Jensen's own pine green irises.

 

The boy had then bit his lower lip, blinking slow once. It was a sign that he was daring Jensen to come over and speak to him—and he might have—had it not been for the client that the boy was with. He watched as the man escorted the boy away, his hand on the perfect curve of his lower back.

 

After that night, Jensen had been hooked—if not borderline obsessed.

 

He _needed_ to know the boy’s name like he needed air. Jensen had then asked around, plucking straws out of the air to see if anyone knew who the boy was. Turns out, he had quite the reputation. According to one of the men that he acted with, he said that the boy—Jared, as his name happened to be—was an escort who had a reasonable price for his company but was worth far more than what his co-star proposed—great companion but an even better fuck.

 

Sex had been one of the last things on Jensen’s mind—surprisingly—upon seeking the boy out. All he wanted was to be in Jared’s company and he found it odd that he wanted his companionship so badly, since he had never spoken to him before. It was very peculiar this feeling he got in his gut when he thought about Jared.

A few days after Jensen was able to get the boy’s contact info, he called and scheduled a time with him. When Jared had asked him where he needed to be escorted to, Jensen said it was a secret. He wasn’t about to take him to a menial charity or dinner party. Jensen wanted to do something different—something he wished Jared would enjoy just as much as himself.

 

And he had found just that.

 

Jensen had given the boy specific directions as to not wear anything spectacular—to which the kid sounded puzzled over the phone—but he had agreed. Jared had shown up to the opera house downtown wearing a slightly baggy, olive green sweatshirt that had HARVARD LAW printed across the front of it in white bolded print, perfect fitting dark washed jeans and a pair of white and black Converse. Jensen had worn his usual attire—consisting of a button-down shirt, dark jeans and polished shoes.

 

When the boy had first shown up, a look of suspicion had glimmered in his eyes. But when Jensen had led him inside and up into a balcony booth, overlooking the groundlings and the stage, there was an excited hum about him. During the performance of _King Lear_ , Jensen hadn’t looked once towards the actors on the stage—not because he didn’t want to, but because he couldn’t.

 

His gaze was solely locked onto Jared.

 

There was a sparkle in his confusing kaleidoscope eyes as the boy watched the play unfold before him. When he smiled, there were dimples in his cheeks and when he laughed, he tossed his head back, letting the humor wash over him.

 

Watching Jared was far more interesting than any play would ever be.

 

Jensen still felt that way even now as the boy straddled his lap, Jared’s hips grinding a slow, sensual rhythm against the erection concealed beneath the layer of denim. His hands were gripping tight but not hard onto the boy’s waist, feeling his hipbones roll forward and back underneath his baggy sweatshirt. Jared had one of his hands pressed against Jensen’s chest, the other one gripping the back of the couch. His head was dipped beside Jensen’s—so close to his ear—that he could hear the soft breathy moans coming from the boy.

 

Jensen felt the boy’s hot mouth against his ear before Jared said, “ _Please_ , Mr. Ackles. Just--” The boy’s fingers twisted in his cotton shirt. “Just let me make you feel good.”

 

Jensen had been holding back all night—holding back from touching him. It’s not that he didn’t want to—because _oh God_ did he want to—but that was not his initial plan. Jensen had paid a substantial sum to spend a night with Jared, but sex was not what he had in mind.  

 

Not originally.

 

Not before the kid started begging him.

 

Jensen could have given in a long time ago, but he held off because he loved the way Jared begged. He had such a pretty way of begging—the high-pitched whine in his throat was difficult for him to resist. Jensen decided ultimately that he had waited long enough.

 

He reached up, slipping his fingers into the boy’s hair and wrenched his head back, exposing the long curve of his esophagus, the cord still hugging his flesh. Jensen ran his teeth, lips and tongue up Jared’s throat and he could feel the boy shudder, sharp gasps falling from his mouth.

Jensen—with his fingers still tight in his hair—pulled Jared closer, his smaller body molding with his own until the boy’s ear was close enough so that he could hear him.

 

“It’s Jensen,” He corrected, his voice low in his throat and the vibration of his tone made Jared whimper.

 

Without warning, Jensen released the boy’s hair and grabbed him up underneath his legs, standing. Jared wrapped his arms around his neck and crossed his ankles around his waist to hold himself up. Jensen walked with the twenty-year old college boy hooked around him, propping his body up against him underneath his rear. The boy hardly weighed anything—his slender build perfect to be man handled.

 

Jensen crawled into the middle of the California king bed, laying Jared against the Egyptian cotton sheets. The boy’s legs were still hiked up around his hips and the Jared was arching his pelvis up against Jensen, wanting to be closer. Jensen looked down at the boy beneath him.

 

Jared’s cheeks, the tip of his nose and his ears were a faint shade of pink from the two glasses of wine he had earlier. His bottom lip was swollen from the bruising kisses. Jared was looking back at him through half lidded eyes, a haze in the kaleidoscope span of them. It was not from the alcohol—Jensen quickly realized—but from sheer and utter _need_ for _him_.

 

Jensen unbuttoned Jared’s jeans and started to slip them—along with his boxers—down his slender thighs. Jared reached down to grab the hem of his sweatshirt, about to remove it as well, when Jensen caught his wrists.

 

“Leave it on,” Jensen instructed. It would ruin his fantasy. He pinned Jared’s wrists above his head. “Keep them here.”

 

Jared did just that, his fingers twisting at the sheets above his head as Jensen slipped his clothes from the rest of his body. Jensen had debated upon keeping the Converse on, but then he removed them, leaving only white socks and the olive sweatshirt left on the boy.

 

Jensen spread the boy’s slender legs. The first thing that caught his attention was a dark mark—like a burn—on the inner part of one of Jared’s thighs. His eyebrows furrowed and he ran a gentle finger against the mark.

 

“Client,” Jared answered softly before Jensen had the chance to ask.

 

A spark of anger ignited in his stomach. He couldn’t understand why someone would want to hurt him—would want to mark him up and leave scars that the boy would have to live with as cruel reminders of someone who had hurt him, who had _wanted_ to hurt him and who got pleasure from it.

 

Jensen lowered himself between the boy’s legs, pressing a soft kiss against the mark on his thigh. He could feel the muscles beneath his skin tremble. Jensen wanted to tell Jared that he would never hurt him, he would never want to leave scars on him, he would never want him in unwanted pain. But he didn’t say any of that because he could tell that Jared didn’t want to hear it nor would he think Jared would believe him anyway.

 

Jensen climbed off the bed for a moment to grab the bottle of lube he had in the drawer beside the bed before returning to Jared once more. He squeezed a small amount in his palm, working the slick liquid between his fingers before Jensen grabbed the boy’s legs under his knees, resting them on his shoulders as he moved forward, pushing them almost all the way to Jared’s chest.  

 

Jensen massaged the pad of his finger against Jared’s hole, trying to relax the muscles. The boy’s fingers twisted into the sheets, a whimper coming from him. Jensen waited until he felt that the muscles were massaged enough before slowly pushing one of his fingers into Jared. Instantly, tight, warm heat clenched around him accompanied by a soft gasp from the boy.

 

“Relax, sweetheart,” Jensen told Jared gently, continuing to slide his finger father into his hole. “I’m not gonna hurt you.”

 

The only sound that Jared made was a whimper, followed by biting his lower lip—a version of understanding.

 

As Jensen worked the boy open, he could see him falling apart. Jared arched his back and whined and gasped and writhed beneath him. His legs trembled up on his shoulders and he continued to work his bottom lip between his teeth.

 

“Need you,” Jared whimpered. “Please, Jensen.”

 

Jensen nodded and placed a light kiss onto the corner of one of Jared’s legs on his shoulders. Removing his fingers, Jensen grabbed for the bottle of lube once more to dab some into his palm. He worked the lube up and down his cock before rubbing the excess off onto Jared’s hole.

 

Careful—as if he’d break him—Jensen started to slide into Jared. The boy suddenly arched up off the bed, his head tossed back and his hands white-knuckled in the sheets.

 

“ _Oh, God_ ,” whined Jared, his voice pitching an octave.

 

A hiss fell past Jensen’s own lips, gritting his teeth as he continued to push into him. Jensen had not expected Jared to be so tight—given his occupation—but he figured it had to do with his age. Jared was only into his first few years of adult hood—not even old enough to legally buy alcohol, but of age to take cock.

 

Jensen slowly built up his speed and the rhythm of his thrusts. Jared had said he wanted to make him feel good, but Jensen wanted to make _him_ feel good—probably for the first time in a long while.

 

Jared’s fingers clenched and unclenched in the sheets. Jensen leaned down, bracing his weight on his hands on either side of the boy’s head.

 

“You can touch me,” Jensen said, sensing the boy’s need for physical contact.

 

Jared quickly obliged, his arms wrapping underneath Jensen’s, his hands on his shoulder blades. Slowly, hands gave way to tips of fingers before his nails dug into his flesh, raking across it. Jared buried his face in the nape of Jensen’s neck and he could feel each hot wisp of air against his sweat slicked skin from each of Jared’s moans or his panting.

 

Jensen could feel Jared’s orgasm building, in the way his inner muscles clenched and his legs locked and quivered around him. When the boy finally came, his entire body jerked, his nails digging hard into his flesh and he cried out. Jensen’s own orgasm followed a minute or so after Jared’s.

 

The next morning, when Jared came wadding sleepily into the dining room, Jensen had been waiting for him. A piece of paper was laid out on the table, a pen neatly placed beside it. As Jensen explained what the paper entailed, he had watched as Jared’s eyes as they widened.

 

The stipulations were quite simple:

 

Jensen would pay for any expenses for the rest of the time Jared was enrolled at Harvard—eight years—and in exchange, Jared would be his escort until his time at Harvard had ended. And he would _only_ be Jensen’s escort.

 

In the end, Jensen had never seen someone sign a contract so fast in his entire life and with such an enthusiastic light about them.

* * *

 


End file.
